$123+ Cheap flights from Chicago (CHI) to Jamaica
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/20. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Jamaica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Chicago to Jamaica
Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated June 12, 2025.
Round-trip from | $329 (Cheapflightsfares) |
|---|---|
One-way from | $123 (FlightHub) |
Popular in | March |
Cheapest in | January |
Average price | $642 |
Good round-trip deal | $523 or less |
Good one-way deal | $242 or less |
Find flight deals from Chicago to Jamaica
Cheapest flights from Chicago to JamaicaExplore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Frontier deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Cheapflightsfares deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This FlightHub deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Booking.com deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Tue 7/1
5:05 am-12:32 pm
1 stop7h 27m
Kingston Norman Manley
Tue 7/8
1:37 pm-11:45 pm
1 stop10h 08m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 9/8
6:00 am-3:36 pm
1 stop9h 36m
Montego Bay Sangster Intl
Sat 9/13
2:23 pm-9:44 pm
1 stop7h 21m
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Tue 7/8
5:05 am-12:32 pm
1 stop7h 27m
Kingston Norman Manley
Tue 7/15
7:05 am-8:55 am
1 stop25h 50m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 7/11
5:40 pm-11:05 am
1 stop17h 25m
Montego Bay Sangster Intl
Tue 7/15
12:10 pm-11:11 pm
2 stops11h 01m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Thu 9/11
6:16 pm-7:53 am
1 stop13h 37m
Montego Bay Sangster Intl
Mon 9/15
9:13 am-1:25 pm
1 stop28h 12m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 6/28
6:16 pm-7:58 am
1 stop13h 42m
Montego Bay Sangster Intl
Wed 7/2
12:07 pm-11:45 pm
1 stop11h 38m
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Tue 8/12
9:10 am-8:25 pm
2 stops11h 15m
Kingston Norman Manley
Tue 8/26
9:25 am-4:28 pm
1 stop7h 03m
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Thu 7/3
10:05 pm-2:30 pm
1 stop16h 25m
Montego Bay Sangster Intl
Thu 7/10
2:26 pm-7:00 pm
Nonstop4h 34m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Fri 7/25
6:40 pm-10:49 am
1 stop16h 09m
Montego Bay Sangster Intl
Fri 8/1
3:53 pm-11:17 pm
1 stop7h 24m
ChicagoMontego Bay
MDW - MBJ
MDWMBJ
Chicago Midway
Mon 6/30
9:00 am-1:00 pm
Nonstop4h 00m
Montego Bay Sangster Intl
Wed 7/9
2:20 pm-6:30 pm
Nonstop4h 10m
Best time to book a flight from Chicago to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Jamaica
What is the cheapest month to book a flight from Chicago to Jamaica?
Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $403). Flying from Chicago to Jamaica in July is currently the most expensive (average of $569). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to JM?
Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.
When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
What is the cheapest day to fly from Chicago to Jamaica?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Jamaica. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Chicago to Jamaica flight should consider departing on Sunday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Jamaica
Explore weekly flight availability from Chicago to Jamaica. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 12, 2025.
The most flights from CHI to JM0 are scheduled on a Monday (2 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
Rainfall in Jamaica by month
Plan your trip to Jamaica by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.
Temperature in Jamaica by month
Plan your trip to Jamaica by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Reviews of airlines servicing Jamaica
Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated June 12, 2025.
See what other customers who have flown with Southwest, Delta and Copa Airlines from Chicago to Jamaica have to say. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Entertainment
Overall
Boarding
Food
Crew
Comfort
Reviews
John,May 2025
PVD - BNA
Related info for your journey
Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Jamaica
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Chicago to Jamaica
Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$276 | Average$426 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$295 | Average$821 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$338 | Average$436 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$410 | Average$621 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$427 | Average$692 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$579 | Average$741 | FlexibilityNo cancel fee | On-time63% |